1614 Dennis St

Key West, FL 33040

$1,499,000
Price
7
Beds
2,699 Sq. Ft.
$555 / Sq. Ft.
2,699
Sq. Ft.
$555
per Sq. Ft.
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virtual-tour-361255-60
a living room with furniture a lamp and a large window
unit a kitchen
a kitchen with a sink a refrigerator and cabinets
a bathroom with a sink mirror and shower
a bedroom with bed and a large mirror
1768508814247_1142
virtual-tour-361255-12
a house with swimming pool in front of it
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a backyard of a house with lots of green space
a living room with furniture and a flat screen tv
a living room with furniture and a table
a kitchen with a sink a refrigerator and cabinets
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a bedroom with a bed and a window
a bathroom with a sink a toilet and shower
a dining room with furniture and window
a kitchen with a sink a refrigerator and window
a living room with furniture and a flat screen tv
a living room with furniture and a flat screen tv
a bathroom with a sink a toilet a mirror and shower curtain
a bedroom with bed and wooden floor
a bedroom with a bed and a chandelier
a bedroom with a bed a dresser and a window
a bathroom with a sink toilet and shower
virtual-tour-361255-32
a view of a chairs and table on the wooden floor
virtual-tour-361255-34
Unit A
Unit B
Upstairs Apt C
1614 Dennis St
virtual-tour-361255-59
a view of a patio with table and chairs potted plants and wooden fence
a kitchen with a refrigerator a stove top oven a sink dishwasher and white cabinets next to a window
virtual-tour-361255-18
a living room with furniture and a flat screen tv
a living room with furniture and a window
a bedroom with a bed and a painting on the wall
a bedroom with a bed and a flat screen tv
a outdoor space with lots of furniture and chandelier
a living room with furniture and a flat screen tv
virtual-tour-361255-37
a kitchen with stainless steel appliances kitchen island granite countertop a sink table and chairs with wooden floor
a living room with furniture and a chandelier
virtual-tour-361255-40
virtual-tour-361255-42
a dining room with furniture and window
virtual-tour-361255-46
a bed room with a bed and a chandelier
a bedroom with a large bed and a window
a bedroom with a bed and a painting on the wall
a bedroom with a bed and a chandelier
a bedroom with a bed and a chandelier
a bedroom with a bed and a dresser in it
a view of backyard with deck and garden
virtual-tour-361255-57
a view of balcony with wooden floor and fence

Description

1614 Dennis St is a rare income-producing triplex offering strong cash flow and flexible use in the heart of Key West. Generating over $125,000 annually in rental income, this well-configured property features three separate units, each with its own washer and dryer, making it highly desirable for long-term tenants and employee housing. The layout includes two spacious 2-bedroom / 1-bath units and an upstairs 3-bedroom / 2-bath residence, providing multiple rental strategies and value-add potential....1614 Dennis St is a rare income-producing triplex offering strong cash flow and flexible use in the heart of Key West. Generating over $125,000 annually in rental income, this well-configured property features three separate units, each with its own washer and dryer, making it highly desirable for long-term tenants and employee housing. The layout includes two spacious 2-bedroom / 1-bath units and an upstairs 3-bedroom / 2-bath residence, providing multiple rental strategies and value-add potential. A standout feature is parking for up to 7 vehicles--a true luxury in Key West and a major draw for tenants. Large Shed on property with two dedicated spaces that could be converted into a workspace. Ideal for investors seeking steady returns or employers looking for quality workforce housing, this triplex combines strong income, practical design, and exceptional parking in one compelling opportunity. Please note some photos were digitally staged and or altered to protect tenant privacy.
  1. Listed by Matthew J Sheehan • Ocean Sotheby's International Realty

Property Details for 1614 Dennis Street

Waterfront
None
Waterfront
No
Zoning
SF - Single Family
Subdivision
New Town - Unrecord (3.0)
Vehicle Storage
Off Street Parking
Pets
Pets Allowed
LISTING UPDATED: 01/20/2026 10:55 AM

Property Details for 1614 Dennis Street

StatusActive
MLS #618151
Days on Market48
Taxes$8,312 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeMulti Family
MLS TypeResidential / Multi-Units
Year Built1968
Lot Size0.12 AC / 5,056 SF
CountyMonroe County
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Location

Listing Courtesy of Ocean Sotheby's International Realty
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Building Information for 1614 Dennis Street

Stories2Residences-Year Built1968Building Size-Lot Size0.12 AC / 5,056 SF

Payment Calculator

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$7,999 per month

30 year fixed, 6.15% Interest

Principal and Interest

$7,306

Property Taxes

$693

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 1614 Dennis Street

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 03 - Key West
  • Absolute Longitude: 81.778453
  • Control Depth: 0
  • Listing Board: Key West Association
  • Side: Median
  • KW Neighborhood: New Town
  • Mile Marker: 3.0
  • Marathon Neighborhood: N/A
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: None
  • Furnished: Unfurnished
  • Tax Year: 2025
  • Tax Exemptions: None
Property
Lot Information
  • Lot Size: 55 X 92
  • Acres: 0.12
  • Parcel #: 00062930-000000
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • Legal: KW DIAG PB 1-13 ALL LT 10 THE SELY 2 FT 4 IN OF LT 13 SQR 4 TR 30 OR300-455/56 OR520-947 OR980-892 OR1089-1773 OR1324-17
  • MLS Approved: Y
  • SqFt Source: Tax Records
  • Flood Zone: AE
  • Rentals Allowed: Yes
  • Deed Restrictions: Unknown
  • Picture Count: 61
  • Document Count: 0
  • Building Style: Above Flood: Unknown
  • Property Condition: Fixer Upper
  • Title: Negotiable
Utilities
  • Utilities: FKAA, Buyer to Verify
  • Pub Sewer HkUp: Yes
  • Pool: No
  • Porch/Balcony: Open Porch/Balcony, Deck
Interior and Exterior Features
Interior Features
  • Floor: Tile, Combo, Vinyl
  • Interior Features: Cathedral Ceilings, Smoke Alarms
  • Appliances: Washer, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof, Combo Roof
  • Construction: CBS, Combo Construction, Frame
  • Dockage: None
  • Exterior Features: Shed

Property History for 1614 Dennis Street

DateEvent & SourcePriceAppreciation
Jan 16, 2026

Listed (Active)

FKMLS #618151

$1,499,000—
Dec 4, 2025

Expired

MiamiRE #A11918981

—
Nov 23, 2025

Listed (Active)

MiamiRE #A11918981

$1,450,000—
Jul 10, 2014

Temp Off Market

FKMLS #115979

—
Jan 24, 2012

Listed (Active)

FKMLS #115979

$675,000—
Jun 23, 2011

Sold (Public Record)

Public Record #311565817

$420,000—
Jun 23, 2011

Sold

FKMLS #110354

$420,000—
Jun 10, 2011

Pending

FKMLS #110354

—
Feb 23, 2009

Listed (Active)

FKMLS #110354

$524,000—
Feb 21, 2009

Expired

FKMLS #107921

—
Feb 20, 2008

Listed (Active)

FKMLS #107921

$559,000—
DateEvent & SourcePrice
01/16/2026

Listed (Active)

FKMLS #618151

$1,499,000
12/04/2025

Expired

MiamiRE #A11918981

—
11/23/2025

Listed (Active)

MiamiRE #A11918981

$1,450,000
07/10/2014

Temp Off Market

FKMLS #115979

—
01/24/2012

Listed (Active)

FKMLS #115979

$675,000
06/23/2011

Sold (Public Record)

Public Record #311565817

$420,000
06/23/2011

Sold

FKMLS #110354

$420,000
06/10/2011

Pending

FKMLS #110354

—
02/23/2009

Listed (Active)

FKMLS #110354

$524,000
02/21/2009

Expired

FKMLS #107921

—
02/20/2008

Listed (Active)

FKMLS #107921

$559,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 1614 Dennis Street

Taxable ValueLand$412,699Additions$392,077Total$804,776
Tax Record2024$7,723 ($644 / month)
Home Facts
Baths4Total Finished SqFt2,699 SqFtAbove Grade Finished SqFt2,699 SqFtStories2Lot Size5,058 SqFtStyleMulti-Family Dwelling (2-4)Year Built1968Year Renovated1993CountyMONROEAPN00062930-000000

Schools near 1614 Dennis Street

This home is within Monroe.
Rating
School
Type
Grades
Distance
Horace O'bryant School
Public - PK to 8
Key West High School
Public - 9 to 12
Somerset Island Prep
Charter - 9 to 12
Lower Keys Academic Connections for Excellence
Public - 6 to 12
Rating
School
Distance
Horace O'bryant School
PublicPK to 8

Key West High School
Public9 to 12

Somerset Island Prep
Charter9 to 12

Lower Keys Academic Connections for Excellence
Public6 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 1614 Dennis Street, Key West, FL 33040

1614 Dennis Street is a multi-family home for sale in Key West, FL 33040. This property was listed for sale on January 16, 2026 by Ocean Sotheby's International Realty, it's currently listed at $1,499,000. It has been on the market for a total of 48 days and was last sold on June 23, 2011. This listing's school district is Monroe. Nearby schools include Horace O'bryant School, Key West High School and Somerset Island Prep. 1614 Dennis Street is a 7-bed, 4-bath, 2,699 sqft multi-family home built in 1968.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Ocean Sotheby's International Realty

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.